Miss Information: When Your Date

"The day before our date I get a text from her informing me that she’s transgender."

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Dear Miss Information,

I am a 32-year-old straight man. For the last six months or so, I’ve been trying online dating. One girl in particular stood out, and for close to a month she and I exchanged emails. It took us a long time to meet because she travels for work. We had a lot in common and I really, really liked this girl. We finally set a date when she was back in town. The day before our date I get a text from her informing me that she’s transgender. So, really, she’s a he. I was pissed and hurt.

I told him I’m not into guys and asked why he didn’t tell me this earlier. He had no response. Our communications got tense and then mostly stopped. I was furious.

This was a week or so ago. I’m still pissed, but I’m starting to feel guilty. I know this is his fault for keeping a secret from me and for pretending to be someone he’s not, but I keep feeling like I handled it badly. I don’t want to hurt his feelings. I just don’t want to date him, and I’m mad that he didn’t tell me sooner.

How do I deal with this weird guilt? I miss talking to this person I thought I was developing feelings for, and I don’t really know how to move on. Thanks,

–Trans Am

Dear Trans Am:

I’m going to take a softball approach, because it seems you’re coming at this from a place of truly wanting to do good, but being largely ignorant of the issues at play here. (Oof, that softball still had some sting. Kind of like getting hit by an actual softball.) Here is the thing: issues of gender and identity are incredibly complex, and many of us are not exposed to them enough to know how to handle their nuances. Fair enough, but that doesn’t mean that discomfort or confusion is an excuse for treating someone recklessly.

For starters, we need to get a few things clear: she is a she, regardless of how she was born. She thinks of herself as a woman; she moves through the world as a woman. You owe her the respect of recognizing her as a woman. And, to that end, she didn’t “pretend to be someone she’s not”—she presented herself as she is. Her femininity may be slightly more complicated than most girls’, but that doesn’t make it less real.

I certainly understand the sting and disappointment that comes from a lost potential-something. However, take a moment to look at the issue from her perspective. Let’s say you’re a cute trans girl. You, like everyone else, want love. You find a great guy online and you hit it off. In the back of your mind, you’re afraid of what he will do when he finds out you haven’t always been female. That’s a tremendous amount of insecurity to hold, and it intensifies the more you grow to like him. Consider, then, that by “handling it badly”, this guy actually reinforces your greatest fear: that your biology is somehow a liability, or that you might be unlovable because of how you were born. So ask yourself, Trans Am, which is worse: the sting of feeling misled and strung along, or the sting of having your very identity rejected?

She told you early on that she is a trans woman. While I understand your hurt, I don’t think she necessarily did anything wrong. I think your guilt speaks to the fact that, deep down, you don’t think she’s at fault, either.

So how do you move on? If they’re sincere, apologies are always nice. Wait till you’re no longer “pissed,” then consider getting back in touch. It took tremendous bravery on her part to tell you at all; the least you can do is thank her for her honesty. After all, you say you miss talking to her. You don’t have to date her, Trans Am, but a connection is a connection. If you’re willing to meet her honesty and admit some vulnerability, you may be able to salvage the situation—and potentially earn a solid friendship.